Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 9, Problem 59P

(a)

Interpretation Introduction

Interpretation:

The stereoisomeric products of (3S, 4S)-3-bromo-4-methylhexane in SN2 reaction with methoxide base should be drawn.

Concept Introduction:

Primary alkyl halide undergoes SN2/E2 reaction: the substitution reaction is favored unless the nucleophile is sterically hindered.

Secondary alkyl halide undergoes SN2/E2 reaction: both the substitution and elimination products reaction are formed. Strong bases bulky bases and high temperature favors the elimination product.

(b)

Interpretation Introduction

Interpretation:

The stereoisomeric products of (3S, 4R)-3-bromo-4-methylhexane in SN2 reaction with methoxide base should be drawn.

Concept Introduction:

Primary alkyl halide undergoes SN2/E2 reaction: the substitution reaction is favored unless the nucleophile is sterically hindered.

Secondary alkyl halide undergoes SN2/E2 reaction: both the substitution and elimination products reaction are formed. Strong bases bulky bases and high temperature favors the elimination product.

(c)

Interpretation Introduction

Interpretation:

The stereoisomeric products of (3R, 4R)-3-bromo-4-methylhexane in SN2 reaction with methoxide base should be drawn.

Concept Introduction:

Primary alkyl halide undergoes SN2/E2 reaction: the substitution reaction is favored unless the nucleophile is sterically hindered.

Secondary alkyl halide undergoes SN2/E2 reaction: both the substitution and elimination products reaction are formed. Strong bases bulky bases and high temperature favors the elimination product.

(d)

Interpretation Introduction

Interpretation:

The stereoisomeric products of (3R, 4S)-3-bromo-4-methylhexane in SN2 reaction with methoxide base should be drawn.

Concept Introduction:

Primary alkyl halide undergoes SN2/E2 reaction: the substitution reaction is favored unless the nucleophile is sterically hindered.

Secondary alkyl halide undergoes SN2/E2 reaction: both the substitution and elimination products reaction are formed. Strong bases bulky bases and high temperature favors the elimination product.

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Where are the chiral centers in this molecule? Also is this compound meso yes or no?
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Where are the chiral centers in this molecule? Also is this compound meso yes or no?

Chapter 9 Solutions

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